N-allyl-2-pyridone-5-carboxylic acid



Patented July 12,v 1949 N-ALLYL-Z-PYRIDONE CARBOXYLIC ACID Lewis A. Walter, East Orange, N. J., assignor to The Maltbie Chemical Company, Newark, N. 3., al corporation of New Jersey No Drawing. Application August 1, 1947, Serial No. 765,625

1 Claim.

My invention relates to a new and useful composition of matter, namely, N-allyl-Z-pyridone- 5-carboxylic acid. This novel compound has the following structural formula:

It is a white crystalline solid, having a melting point of 152-153 C. uncorrected.

This compound is useful as an intermediate in the preparation of certain therapeutically useful compounds.

One method of preparation of this novel compound which has been successfully performed is as follows:

Two hundred-ninety grams of methyl coumalinate was suspended in 750 ml. of alcohol and stirred in an ice bath while 250 ml. of allylamine was slowly added. The mixture was then stirred for twenty minutes at room temperature. A solution of 400 g. of potassium hydroxide in 1200 ml. of water was next added and the solution was refluxed vigorously for twenty minutes, then cooled and immediately acidified to Congo red with concentrated hydrochloric acid. On cooling potassium chloride and the N-allyl-2-pyridone-5-carboxylic acid precipitated andwas filtered off. This mixture was recrystallized from water with the use of a little charcoal, to give white crystals of N-al1yl-2pyridone-5-carboxylic acid, of M. P. 152-153 C. uncorrected.

What I claim is:

As a novel and useful composition of matter, the chemical compound, N-allyl-2-pyridone-5- carboxylic acid having the structural formula:

HOE

AIHPC H=C HI LEWIS A. WALTER.

REFERENCES CITED UNITED STATES PATENTS Name Date Boese Jan. 2, 1940 OTHER REFERENCES Zeit. fiir Angew. Chem, 44, 836 (1931). Von Pechmann: Berichte, 17, 2391.

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